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Maytenus aquifolium

(previously named: Maytenus aquifolia; later renamed to: Monteverdia aquifolia)
(NCBI TaxID 1081512, species name lookup)

Taxonomic group: plant / Streptophyta (Phylum: Streptophyta)
Organ / tissue: leaf

The structure was elucidated in this paper
NCBI PubMed ID: 10563907
Publication DOI: 10.1021/jf980114i
Journal NLM ID: 0374755
Publisher: American Chemical Society
Institutions: Instituto de Quimica de Araraquara, Universidade Estadual Paulista, C. Postal 355, 14801-970 Araraquara, SP, Brazil, and Dipartimento di Scienze Farmaceutiche, Università degli Studi di Salerno, Piazza Vittorio Emanuele 9, 84084 Penta di Fisciano (SA), Italy

Droplet countercurrent chromatography and high-performance liquid chromatography fractionation of the aqueous infusion from Maytenus aquifolium Martius leaves afforded two flavonoid tetrasaccharides: quercetin 3-O-α-L-rhamnopyranosyl(1→6)-O-[β-D-glucopyranosyl(1→3)-O-α-L-rhamnopyranosyl(1→2)-O-β-D-galactopyranoside and kaempferol 3-O-α-L-rhamnopyranosyl(1→6)-O-[β-D-glucopyranosyl(1→3)-O-α-L-rhamnopyranosyl(1→2)-O-β-D-galactopyranoside. All structures were elucidated by spectroscopic methods. Pharmacological essays of the infusion showed antiulcer activity in rats.

infusion, flavonoid glycosides, Celastraceae, Maytenus aquifolium Martius, espinheira santa, antiulcer acitivity, 1D and 2D NMR

Structure type: oligomer ; 917 [M-H]-
C₃₉H₅₀O₂₅
Location inside paper: compound 1, fig. 1(1), table 1(1), table 2(1)
Compound class: flavonol glycoside
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88

Methods: 13C NMR, 1H NMR, IR, TLC, HPLC, UV, EI-MS, HMBC, DEPT, COSY, HOHAHA, HSQC, HCl hydrolysis, HCl methanolysis, DFQ-COSY, DCCC, antiulcer tests
Biological activity: Compound 1 showed dose-dependent effect of the infusion of M. aquifolium on stress-induced gastric ulcers on rats.
Comments, role: NMR temperature was not specified

Related record ID(s): 62911
NCBI Taxonomy refs (TaxIDs): 1081512
Show glycosyltransferases

NMR conditions: in CD3OD [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16
3,2,3	bDGlcp	105.7	75.3	77.3	69.7	77.2	62.2
3,2	aLRhap	101.8	72.0	83.0	72.7	70.7	17.6
3,6	aLRhap	102.2	72.2	71.6	73.8	69.6	17.9
3	bDGalp	101.1	77.2	75.6	71.0	75.4	67.0
	xXQuercetin	-	158.3	134.5	179.3	163.0	99.7	165.6	94.6	158.5	105.8	123.2	117.4	145.8	149.6	116.1	123.0


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16
3,2,3	bDGlcp	4.59	3.36	3.43	3.64	3.39	3.76-3.90
3,2	aLRhap	5.29	4.32	3.98	3.57	4.15	1.04
3,6	aLRhap	4.59	3.56	3.81	3.32	3.43	1.18
3	bDGalp	5.64	3.97	3.74	3.49	3.44	3.48-3.72
	xXQuercetin	-	-	-	-	-	6.22	-	6.41	-	-	-	7.75	-	-	6.94	7.61


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9	C10/H10	C11/H11	C12/H12	C13/H13	C14/H14	C15/H15	C16/H16
3,2,3	bDGlcp	105.7/4.59	75.3/3.36	77.3/3.43	69.7/3.64	77.2/3.39	62.2/3.76-3.90
3,2	aLRhap	101.8/5.29	72.0/4.32	83.0/3.98	72.7/3.57	70.7/4.15	17.6/1.04
3,6	aLRhap	102.2/4.59	72.2/3.56	71.6/3.81	73.8/3.32	69.6/3.43	17.9/1.18
3	bDGalp	101.1/5.64	77.2/3.97	75.6/3.74	71.0/3.49	75.4/3.44	67.0/3.48-3.72
	xXQuercetin						99.7/6.22		94.6/6.41				117.4/7.75			116.1/6.94	123.0/7.61

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H8	H12	H15	H16
3,2,3	bDGlcp	4.59	3.36	3.43	3.64	3.39	3.76 3.90
3,2	aLRhap	5.29	4.32	3.98	3.57	4.15	1.04
3,6	aLRhap	4.59	3.56	3.81	3.32	3.43	1.18
3	bDGalp	5.64	3.97	3.74	3.49	3.44	3.48 3.72
	xXQuercetin						6.22	6.41	7.75	6.94	7.61

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16
3,2,3	bDGlcp	105.7	75.3	77.3	69.7	77.2	62.2
3,2	aLRhap	101.8	72.0	83.0	72.7	70.7	17.6
3,6	aLRhap	102.2	72.2	71.6	73.8	69.6	17.9
3	bDGalp	101.1	77.2	75.6	71.0	75.4	67.0
	xXQuercetin		158.3	134.5	179.3	163.0	99.7	165.6	94.6	158.5	105.8	123.2	117.4	145.8	149.6	116.1	123.0

The spectrum also has 1 signal at unknown position (not plotted).

There is only one chemically distinct structure:

C[C@@H]1O[C@@H](O[C@H]2[C@H](Oc3c(-c4ccc(O)c(O)c4)oc4cc(O)cc(O)c4c3=O)O[C@H](CO[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@H](O)[C@@H]2O)[C@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O

SVG MW SMILES 3D mol Ionize

Maytenus aquifolium

(previously named: Maytenus aquifolia; later renamed to: Monteverdia aquifolia)
(NCBI TaxID 1081512, species name lookup)

infusion, flavonoid glycosides, Celastraceae, Maytenus aquifolium Martius, espinheira santa, antiulcer acitivity, 1D and 2D NMR

Structure type: oligomer ; 901 [M-H]-
C₃₉H₅₀O₂₄
Location inside paper: compound 2, fig. 1(2), table 1(2), table 2(2)
Compound class: flavonol glycoside
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88

Methods: 13C NMR, 1H NMR, IR, TLC, HPLC, UV, EI-MS, HMBC, DEPT, COSY, HOHAHA, HSQC, HCl hydrolysis, HCl methanolysis, DFQ-COSY, DCCC, antiulcer tests
Biological activity: Compound 2 showed dose-dependent effect of the infusion of M. aquifolium on stress-induced gastric ulcers on rats.
Comments, role: NMR temperature was not specified

Related record ID(s): 62910
NCBI Taxonomy refs (TaxIDs): 1081512
Show glycosyltransferases

NMR conditions: in CD3OD [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16
3,2,3	bDGlcp	105.8	75.4	77.5	69.8	77.2	62.4
3,2	aLRhap	101.9	72.1	83.0	72.8	70.7	17.8
3,6	aLRhap	102.2	72.3	71.6	74.0	69.7	17.9
3	bDGalp	101.3	77.6	75.4	71.0	75.3	67.2
	xXKaempferol	-	158.3	134.5	179.4	163.1	99.8	165.8	94.7	158.3	105.8	122.9	132.2	116.2	161.2	116.2	132.2


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16
3,2,3	bDGlcp	4.59	3.36	3.42	3.64	3.38	3.76-3.89
3,2	aLRhap	5.26	4.31	3.96	3.56	4.15	1.03
3,6	aLRhap	4.54	3.54	3.79	3.30	3.41	1.18
3	bDGalp	5.55	3.96	3.72	3.48	3.42	3.47-3.72
	xXKaempferol	-	-	-	-	-	6.23	-	6.42	-	-	-	8.07	6.93	-	6.93	8.07


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9	C10/H10	C11/H11	C12/H12	C13/H13	C14/H14	C15/H15	C16/H16
3,2,3	bDGlcp	105.8/4.59	75.4/3.36	77.5/3.42	69.8/3.64	77.2/3.38	62.4/3.76-3.89
3,2	aLRhap	101.9/5.26	72.1/4.31	83.0/3.96	72.8/3.56	70.7/4.15	17.8/1.03
3,6	aLRhap	102.2/4.54	72.3/3.54	71.6/3.79	74.0/3.30	69.7/3.41	17.9/1.18
3	bDGalp	101.3/5.55	77.6/3.96	75.4/3.72	71.0/3.48	75.3/3.42	67.2/3.47-3.72
	xXKaempferol						99.8/6.23		94.7/6.42				132.2/8.07	116.2/6.93		116.2/6.93	132.2/8.07

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H8	H12	H13	H15	H16
3,2,3	bDGlcp	4.59	3.36	3.42	3.64	3.38	3.76 3.89
3,2	aLRhap	5.26	4.31	3.96	3.56	4.15	1.03
3,6	aLRhap	4.54	3.54	3.79	3.30	3.41	1.18
3	bDGalp	5.55	3.96	3.72	3.48	3.42	3.47 3.72
	xXKaempferol						6.23	6.42	8.07	6.93	6.93	8.07

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16
3,2,3	bDGlcp	105.8	75.4	77.5	69.8	77.2	62.4
3,2	aLRhap	101.9	72.1	83.0	72.8	70.7	17.8
3,6	aLRhap	102.2	72.3	71.6	74.0	69.7	17.9
3	bDGalp	101.3	77.6	75.4	71.0	75.3	67.2
	xXKaempferol		158.3	134.5	179.4	163.1	99.8	165.8	94.7	158.3	105.8	122.9	132.2	116.2	161.2	116.2	132.2

The spectrum also has 1 signal at unknown position (not plotted).

There is only one chemically distinct structure:

C[C@@H]1O[C@@H](O[C@H]2[C@H](Oc3c(-c4ccc(O)cc4)oc4cc(O)cc(O)c4c3=O)O[C@H](CO[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@H](O)[C@@H]2O)[C@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O

SVG MW SMILES 3D mol Ionize